FI61694C - Foerfarande foer framstaellning av substituerade arylalkylaminer med blodtrycket och hjaertslagfrekvensen saenkande verkan - Google Patents
Foerfarande foer framstaellning av substituerade arylalkylaminer med blodtrycket och hjaertslagfrekvensen saenkande verkan Download PDFInfo
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- FI61694C FI61694C FI760465A FI760465A FI61694C FI 61694 C FI61694 C FI 61694C FI 760465 A FI760465 A FI 760465A FI 760465 A FI760465 A FI 760465A FI 61694 C FI61694 C FI 61694C
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- FI
- Finland
- Prior art keywords
- group
- general formula
- dimethoxy
- phthalimidine
- chlorine
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- 210000004369 blood Anatomy 0.000 title 1
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- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- HJBBKVHYQQUPQW-UHFFFAOYSA-N 3-chloro-n-[2-(3,4-dimethoxyphenyl)ethyl]-n-methylpropan-1-amine Chemical compound COC1=CC=C(CCN(C)CCCCl)C=C1OC HJBBKVHYQQUPQW-UHFFFAOYSA-N 0.000 description 1
- VZGITQAWSRBJPP-UHFFFAOYSA-N 4-(2-chloroethyl)-1,2-dimethoxybenzene Chemical compound COC1=CC=C(CCCl)C=C1OC VZGITQAWSRBJPP-UHFFFAOYSA-N 0.000 description 1
- SUIQIOALWGAJCD-UHFFFAOYSA-N 5,6-dimethoxy-1,1-dioxo-1,2-benzothiazol-3-one Chemical compound C1=C(OC)C(OC)=CC2=C1S(=O)(=O)NC2=O SUIQIOALWGAJCD-UHFFFAOYSA-N 0.000 description 1
- YEWAFZBPGRDDEV-UHFFFAOYSA-N 5,6-dimethoxy-1,2-benzothiazole 1,1-dioxide Chemical compound C1=C(OC)C(OC)=CC2=C1S(=O)(=O)N=C2 YEWAFZBPGRDDEV-UHFFFAOYSA-N 0.000 description 1
- JQWWRDNCIIOJIL-UHFFFAOYSA-N 5-chloro-2-(3-chloropropyl)-3-phenyl-3h-1,2-benzothiazole 1,1-dioxide Chemical compound C12=CC(Cl)=CC=C2S(=O)(=O)N(CCCCl)C1C1=CC=CC=C1 JQWWRDNCIIOJIL-UHFFFAOYSA-N 0.000 description 1
- XBLUCWQAMXHBTM-UHFFFAOYSA-N 6-(3-chloropropyl)-[1,3]dioxolo[4,5-f]isoindole-5,7-dione Chemical compound C1=C2C(=O)N(CCCCl)C(=O)C2=CC2=C1OCO2 XBLUCWQAMXHBTM-UHFFFAOYSA-N 0.000 description 1
- PMYRXZZLJTVWOX-UHFFFAOYSA-N 7-(3-chloropropyl)-2,3-dihydro-[1,4]dioxino[2,3-f]isoindole-6,8-dione Chemical compound O1CCOC2=C1C=C1C(=O)N(CCCCl)C(=O)C1=C2 PMYRXZZLJTVWOX-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- BZVRKWXGBKHMMG-UHFFFAOYSA-N COC=1C=C(C=CC1OC)N(CCCN)CCC Chemical compound COC=1C=C(C=CC1OC)N(CCCN)CCC BZVRKWXGBKHMMG-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 241001071900 Scapanus orarius Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- UBAZGMLMVVQSCD-UHFFFAOYSA-N carbon dioxide;molecular oxygen Chemical compound O=O.O=C=O UBAZGMLMVVQSCD-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- LDAUBLFTYKFIOQ-UHFFFAOYSA-N methyl 2-(bromomethyl)-4,5-dimethoxybenzoate Chemical compound COC(=O)C1=CC(OC)=C(OC)C=C1CBr LDAUBLFTYKFIOQ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- RCYQJSASQWXACC-UHFFFAOYSA-N n'-[2-(3,4-dimethoxyphenyl)ethyl]-n'-methylethane-1,2-diamine Chemical compound COC1=CC=C(CCN(C)CCN)C=C1OC RCYQJSASQWXACC-UHFFFAOYSA-N 0.000 description 1
- JWANNLXCVGJLAS-UHFFFAOYSA-N n'-[2-(3,4-dimethoxyphenyl)ethyl]-n'-methylpropane-1,3-diamine Chemical compound COC1=CC=C(CCN(C)CCCN)C=C1OC JWANNLXCVGJLAS-UHFFFAOYSA-N 0.000 description 1
- ZLPVHRHKOAFZMH-UHFFFAOYSA-N n'-[2-(3,4-dimethoxyphenyl)ethyl]propane-1,3-diamine Chemical compound COC1=CC=C(CCNCCCN)C=C1OC ZLPVHRHKOAFZMH-UHFFFAOYSA-N 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
- C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2509797A DE2509797C2 (de) | 1975-03-06 | 1975-03-06 | Phthalimidine, deren physiologisch verträgliche Säureadditionssalze, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DE2509797 | 1975-03-06 | ||
| DE2558273 | 1975-12-23 | ||
| DE2558274 | 1975-12-23 | ||
| DE19752558274 DE2558274A1 (de) | 1975-12-23 | 1975-12-23 | Neue substituierte arylalkylamine |
| DE19752558273 DE2558273A1 (de) | 1975-12-23 | 1975-12-23 | Neue verfahren zur herstellung von arylalkylaminen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI760465A7 FI760465A7 (en, 2012) | 1976-09-07 |
| FI61694B FI61694B (fi) | 1982-05-31 |
| FI61694C true FI61694C (fi) | 1982-09-10 |
Family
ID=27186298
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI760465A FI61694C (fi) | 1975-03-06 | 1976-02-24 | Foerfarande foer framstaellning av substituerade arylalkylaminer med blodtrycket och hjaertslagfrekvensen saenkande verkan |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS51113866A (en, 2012) |
| AU (1) | AU498958B2 (en, 2012) |
| CA (1) | CA1073915A (en, 2012) |
| CH (1) | CH621340A5 (en, 2012) |
| DD (1) | DD123741A5 (en, 2012) |
| DK (1) | DK138792C (en, 2012) |
| ES (1) | ES445812A1 (en, 2012) |
| FI (1) | FI61694C (en, 2012) |
| FR (1) | FR2302733A1 (en, 2012) |
| GB (1) | GB1503625A (en, 2012) |
| GR (1) | GR60053B (en, 2012) |
| HK (1) | HK46881A (en, 2012) |
| IE (1) | IE42962B1 (en, 2012) |
| IL (1) | IL49150A (en, 2012) |
| LU (1) | LU74479A1 (en, 2012) |
| MX (1) | MX3393E (en, 2012) |
| NL (1) | NL7601796A (en, 2012) |
| NO (1) | NO144212C (en, 2012) |
| PT (1) | PT64873B (en, 2012) |
| SE (1) | SE418398B (en, 2012) |
| SU (1) | SU620209A3 (en, 2012) |
| YU (3) | YU40642B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3242477A1 (de) * | 1982-11-18 | 1984-05-24 | Basf Ag, 6700 Ludwigshafen | Heterocyclisch substituierte nitrile, ihre herstellung und verwendung als arzneimittel |
| GB8609331D0 (en) * | 1986-04-16 | 1986-05-21 | Pfizer Ltd | Anti-arrythmia agents |
| US5567718A (en) * | 1994-08-11 | 1996-10-22 | Hoechst Marion Roussel Inc. | 2,3-dihydro-1h-isoindole derivatives and their use as serotonin reuptake inhibitors |
| CZ302807B6 (cs) | 2000-05-25 | 2011-11-23 | F. Hoffmann-La Roche Ag | Substituovaný 1-aminoalkyllaktam, zpusob jeho prípravy a použití pro výrobu léciva a farmaceutická kompozice s jeho obsahem |
-
1976
- 1976-02-18 DD DD191310A patent/DD123741A5/xx unknown
- 1976-02-23 NL NL7601796A patent/NL7601796A/xx unknown
- 1976-02-24 FI FI760465A patent/FI61694C/fi not_active IP Right Cessation
- 1976-02-24 GR GR50141A patent/GR60053B/el unknown
- 1976-02-25 SU SU762325959A patent/SU620209A3/ru active
- 1976-02-27 SE SE7602856A patent/SE418398B/xx not_active IP Right Cessation
- 1976-03-03 CH CH266676A patent/CH621340A5/de not_active IP Right Cessation
- 1976-03-03 IE IE439/76A patent/IE42962B1/en unknown
- 1976-03-04 JP JP51023699A patent/JPS51113866A/ja active Granted
- 1976-03-04 IL IL49150A patent/IL49150A/xx unknown
- 1976-03-04 LU LU74479A patent/LU74479A1/xx unknown
- 1976-03-04 DK DK92876A patent/DK138792C/da active
- 1976-03-04 YU YU550/76A patent/YU40642B/xx unknown
- 1976-03-05 GB GB8961/76A patent/GB1503625A/en not_active Expired
- 1976-03-05 CA CA247,229A patent/CA1073915A/en not_active Expired
- 1976-03-05 NO NO760766A patent/NO144212C/no unknown
- 1976-03-05 PT PT64873A patent/PT64873B/pt unknown
- 1976-03-05 MX MX000041U patent/MX3393E/es unknown
- 1976-03-05 FR FR7606435A patent/FR2302733A1/fr active Granted
- 1976-03-05 ES ES445812A patent/ES445812A1/es not_active Expired
-
1978
- 1978-03-05 AU AU11729/76A patent/AU498958B2/en not_active Expired
-
1981
- 1981-09-17 HK HK468/81A patent/HK46881A/xx unknown
-
1982
- 1982-05-07 YU YU00981/82A patent/YU98182A/xx unknown
- 1982-05-07 YU YU00980/82A patent/YU98082A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: DR. KARL THOMAE GESELLSCHAFT MIT |